Benyltrimethylammonium tetrachloroiodate → N-(1-Benzyl-8-chloro-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of compound 165A (121 mg, 0.3 mmol) in acetic acid (2 mL) at RT was added benzyltrimethylammonium tetrachloroiodate (125.7 mg, 0.3 mmol). The reaction mixture was stirred at RT for 30 min, and then concentrated under reduced pressure. The resultant residue was partitioned between saturated aqueous NaHCO3 solution and CH2Cl2. The separated aqueous layer was extracted with CH2Cl2 (15 mL×2). The combined CH2Cl2 extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified using preparative HPLC (YMC S5 ODS 20×100 mm) eluting with MeOH (50-80%) in H2O for 8 min, and then 80% MeOH in H2O for 7 min to give the title compound (108 mg, 82%) as a white solid. HPLC: 99% at 7.65 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O−10% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 438 [M+H]+.

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